5 Hats to Wear to the Kentucky Derby, Plus More Derby Fashion Tips

It’s off to the races once again, as the Kentucky Derby is going down Saturday, May 4, 2024, at Churchill Downs in Louisville, Kentucky. Although fans attend the festivities to experience the most exciting two minutes in sports, a big element of all the fun is the Kentucky Derby fashion.

The Derby provides an excuse for attendees to get all dressed up in their most dapper garb, and there’s only one fashion rule to follow: There’s no such thing as too much.

Indeed, Kentucky Derby fashion is all about making a statement. Going over-the-top is highly encouraged, and a top-notch Derby day ensemble begins with the hat, of course.

Types of Kentucky Derby Hats

From wide-brimmed hats to fascinators, here are five over-the-top options that are guaranteed to turn heads at the 150th Kentucky Derby — along with tips on how to style your Derby topper.

1. Classic Wide-Brimmed Sunhat

When it comes to Derby hats for women, wide-brimmed is the most popular choice, and this feather-topped ivory hat from Etsy is the epitome of Derby fashion. It’s perfect if you’re drawn to more neutral colors, but still want to stand out.

2. Fancy Fascinator

If you want to make a statement without getting too extravagant, this neutral straw headpiece from Vineyard Vines is what Kentucky Derby fashion dreams are made of. It’s got it all: delicate feathers, ribbon detailing, and a demure veil.

3. Crown Jewels

Not feeling shy about your Derby headwear? With its sparkling gold accents and dazzling blue feathers, this fascinator from Aimee Fuller really nails the drama.

4. Pretty Peacock

Is it even a Kentucky Derby fashion round-up if there’s no hat adorned with a peacock feather? We think not. The rich, royal emerald color of this hat from Etsy makes it even more of a stunner.

5. Beautiful Butterfly

Only one word comes to mind when you see this custom butterfly headpiece from Etsy: wow. That’s how you make a statement at the Kentucky Derby.

How to Style Your Kentucky Derby Hat

The hard part is done — you’ve got your stunning topper; now it’s time to complete the ensemble. With that, here are five tips on how to style your Derby hat.

1. Go wild with patterns

The Kentucky Derby is not the occasion to be demure with your hat choice or ensemble. Pair your over-the-top hat with a dress or suit in a standout pattern — think stripes, gingham, florals, or plaid.

2. Add pops of color

The same goes for color — leave the beige at home. The Kentucky Derby is the perfect time to bust out pieces in bright, vibrant hues or dreamy pastels. And if you feel like being bold, go for a head-to-toe monochromatic look in your favorite color.

3. Wear comfortable shoes

Although the actual race only lasts a few minutes, the Kentucky Derby is a whole day event, so wearing comfortable shoes is a must. For the ladies, summer sandals with a chunky heel, espadrille wedges, or a delicate lace pump are great options. For the gents, you can’t go wrong with a pair of loafers or oxfords.

4. Go for hat alternatives

Yes, big hats are the name of the game when it comes to Kentucky Derby fashion, but there are other alternatives if a more toned-down yet festive look is more your vibe. After you’ve snapped pics of yourself modeling your showstopper, you can ditch the big hat and change into something more comfortable: Cute headbands, bowlers, fedoras, and pork pie hats are all acceptable. Don’t be afraid to think outside the (hat) box!

5. Have fun with accessories

Your Derby Day look isn’t complete without the right accessories. Bowties in bright colors, prints, or patterns are an easy way to jazz up your look. Classic jewelry like pearl earrings make a fine choice. For handbags, a charming straw tote fits right in. Just be sure it’s easy to carry on race day and adheres to purse size limitations.